While legendary buccaneers such as Blackbeard and Calico Jack often dominate popular imagination, a shadowy roster of lesser‑known marauders also carved a permanent scar into the annals of seafaring horror. In this roundup of 10 history s, we shine a lantern on those fearsome captains whose ruthless deeds still echo across the waves.
10 History S: The Most Brutal Buccaneers
10 Sadie The Goat
Sadie Farrell, a notorious gang chief hailing from New York’s underbelly, earned a reputation for driving her victims to the brink by head‑butting them straight into the gut before stripping them blind. Though her early criminal career involved petty theft, a dramatic encounter with the Charlton Street Gang’s botched sloop robbery ignited her ambition to become a pirate. Within days, she leapt into the fray, leading a daring seizure of a far larger vessel.
Her crew quickly became infamous for their coarse language and reckless daring, cruising the Hudson and Harlem Rivers to plunder other ships, raid coastal settlements, and snatch people for ransom. Tales of prisoners being forced to “walk the plank” circulated alongside the grisly legend of Sadie sporting a human ear around her neck – a gruesome trophy bitten off a rival gangster during a violent clash.
The Goat’s marauding reign persisted for several months until a coalition of local farmers amassed enough force to push them back. Defeated, Sadie retreated to land, yet her legacy endured, forever branding her as the “Queen of the Waterfront” in New York folklore.
9 Francois L’Olonnais
Born Jean‑David Nau to a destitute French family in the 1600s, Francois l’Olonnais was thrust into indentured servitude before eventually escaping to the bustling colony of Saint‑Domingue (present‑day Haiti). There, he immersed himself in the chaotic world of buccaneers, targeting Spanish‑laden vessels plying the West Indies trade routes.
After a disastrous shipwreck that left his crew brutally assaulted by Spanish troops, l’Olonnais swore vengeance. He rallied the surviving men on Tortuga, where they unleashed a savage raid that razed the town and annihilated an entire rescue party dispatched by the governor of Havana. Only a single sailor was spared, forced to bear witness to the carnage.
His notoriety stemmed largely from his love of torture. Among his favorite methods were cleaving chunks of flesh from captives with his sword and a gruesome technique called “woolding,” wherein a rope was tightened around a victim’s skull until the eyes burst forth.
Fleeing a renewed Spanish assault, l’Olonnais inadvertently grounded his crippled ship along Panama’s coast. While his men scrounged for provisions, they fell into the hands of the native Kuna tribe—cannibals who devoured both the pirate and his remaining crew, ending his reign of terror.
8 Nicholas Brown
Nicholas Brown, dubbed “The Grand Pirate” by his contemporaries, prowled the waters off Jamaica in the early 1700s. Though details of his youth remain murky, he quickly earned infamy by raiding English, Portuguese, and Spanish vessels throughout the Caribbean, amassing a fearsome reputation.
In a bid to curtail his depredations, colonial authorities extended a royal pardon, hoping to lure him back into lawful society. Brown initially accepted, but the allure of piracy proved too strong; he soon abandoned the straight‑and‑narrow life, prompting the Jamaican government to post a £500 bounty on his head.
His old schoolmate and naval adversary, John Drudge, seized upon the bounty with literal fervor. After tracking down Brown, Drudge slayed him, then decapitated his friend, preserved the head in a rum‑filled keg, and marched back to Jamaica to claim his reward, cementing a grisly episode in pirate lore.
7 The Victual Brothers
The Victual Brothers originated as a cadre of German mercenaries hired by King Albert of Sweden to wage war against Denmark during the 14th‑century conflicts. Rather than simply seizing enemy ships for the crown, the group swiftly morphed into a Robin Hood‑style fleet, plundering opulent merchant vessels to feed the starving and support the downtrodden.
During the siege of Stockholm by Queen Margaret of Denmark, the Victual Brothers executed a bold breakout, slicing through the blockade to deliver vital provisions, ammunition, and military aid to the beleaguered city’s populace.
Emboldened by their success, they established a permanent base on Gotland Island, turning the icy Baltic waters into a hunting ground. Their relentless attacks on any ship they encountered caused such panic among merchants and state vessels that Baltic trade ground to a near‑standstill.
In response, King Albert and Queen Margaret temporarily set aside their rivalry to jointly expel the marauders. By 1400, royal forces captured Klaus Stortebeker, a principal leader, and brought him to trial in Hamburg, where he met a swift beheading.
With Stortebeker’s execution, the remaining Victual Brothers were systematically hunted down and eradicated by Danish and Swedish authorities, ending their reign of terror in the Baltic Sea.
6 Edward Jordan
Edward Jordan’s brief yet ferocious piratical career began amid the Irish rebellion against the British Crown in 1798. Captured and sentenced to hang, he escaped, was recaptured, and ultimately bought his freedom by trading valuable insurgent intelligence for a royal pardon.
When Irish compatriots discovered his betrayal, Jordan fled across the Atlantic, settling in Gaspé where he secured a loan to purchase a schooner named Three Sisters. His inability to repay the debt led creditors to dispatch Captain Stairs in 1809 to seize the vessel.
Initially, Jordan appeared compliant, even requesting passage for his family aboard the schooner to secure honest employment. However, once the ship set sail, he brandished a pistol, attempted to shoot Captain Stairs, missed, and instead killed the first mate. Stairs escaped by leaping overboard.
Jordan commandeered the Three Sisters, steering toward Newfoundland with plans to recruit a new crew and flee back to Ireland. Yet a passing ship rescued Stairs, prompting a swift search for Jordan’s vessel. A bounty of £100 was offered for the capture of “Pirate Jordan.”
The schooner was intercepted off Newfoundland’s coast, and Jordan was tried, condemned to death, and his body tarred and displayed in chains at the harbor as a stark warning to other seafarers.
5 Edward Low
Edward Low entered the world in London as the son of a destitute family, turning to petty theft from a young age. After an early marriage, he and his wife ventured to the New World, only for her to die in childbirth, prompting Low to return to a life of crime.
He earned his pirate mantle after leading a mutiny aboard a sloop bound for Honduras, where he had been employed as a rigger. Unlike many of his contemporaries, Low kept his fleet modest—typically three or four ships—yet his cruelty knew no bounds.
Following a successful capture, Low would torture his captives before setting the seized vessel ablaze. Crew member Philip Aston recalled Low’s barbarity, noting that no English crew matched his savage reputation. Low’s preferred method involved binding a victim’s hands, threading rope between the fingers, then igniting the rope, scorching the flesh to the bone.
He also delighted in brutal cutlass assaults, famously cutting off the lips of the captain of the Portuguese ship Nostra Signiora de Victoria and subsequently broiling and force‑feeding them to the horrified captain. Low’s ferocity and reckless tactics made him the most feared pirate of the early 1700s, though his ultimate fate remains a mystery—rumors suggest a storm‑driven wreck, mutiny, or French capture and execution.
4 Black Caesar
Black Caesar, a towering figure reputed to have once been an African chieftain, was captured and shipped to the Americas as a slave. After a shipwreck off Florida’s coast, he and a companion commandeered a longboat, escaping the sinking vessel.
Disguised as shipwreck survivors, they lured passing vessels, then seized them at gunpoint, demanding provisions and valuables. Caesar amassed a modest fortune, which he allegedly buried on Elliot Key.
He later expanded his operations by capturing a larger ship and recruiting a crew, allowing him to venture into deeper waters while still haunting the Florida Keys. Ingeniously, he devised a method of submerging his boat beneath the surface using a rope and a stone‑set metal ring, rendering it invisible to coastal patrols.
In the early 18th century, Caesar joined the infamous Blackbeard’s crew as a lieutenant aboard the Queen Anne’s Revenge. After Blackbeard’s demise, Virginia authorities apprehended Caesar, sentencing him to death by hanging. To this day, treasure hunters scour Elliot Key, hoping to uncover the lost loot.
3 Henry Every
Henry Every, also known as “Long Ben” or “The King of Pirates,” orchestrated the most lucrative pirate raid ever recorded—equivalent to roughly $78 million today—before vanishing without a trace.
He began his maritime career in Britain’s Royal Navy, serving during the Nine Years’ War. After the conflict, he joined the merchant vessel Charles II, sailing to the West Indies to intercept French ships. A sluggish season left the crew restless, culminating in a mutiny that elevated Every to captain and rechristened the ship the Fancy.
Renowned for masterful ambush tactics and deft navigation, Every pillaged several English and Danish vessels before learning of a massive Indian convoy. He steered the Fancy toward the island of Perim, where he allied with pirate Thomas Tew and other local buccaneers to intercept the fleet of 25 Indian ships.
During the clash, Tew perished, and many pirate ships lagged behind. Undeterred, Every pursued the two largest ships, overtook them, and seized a treasure trove, allowing his crew to indulge in rampant rape, pillage, and torture. He then fled across the Atlantic, briefly anchoring near Nassau before setting sail for good.
After departing the Bahamas, Every, his crew, and the astounding loot disappeared, eluding the East India Company’s manhunt and cementing his legend as a phantom pirate.
2 Bartholomew Roberts
Bartholomew Roberts, famed as “Black Bart,” claimed over 400 vessels during his illustrious career, making him one of history’s most successful pirates. In 1719, while serving aboard the slave ship Princess, the vessel fell to a pirate attack off West Africa, and Roberts was swiftly drafted into the crew due to his exceptional navigational skills.
His ascent was rapid; after the captain perished in battle, Roberts was elected leader. Commanding the flagship Royal Fortune, he pursued and seized larger, better‑armed British, Portuguese, and Spanish warships with ruthless efficiency.
Roberts’ treatment of captives was chillingly pragmatic. After overtaking a slave ship carrying 80 chained Africans, he burned the vessel without freeing the prisoners. In a separate vendetta against the governor of Martinique, Roberts boarded a ship, murdered the governor, and displayed the corpse on the Royal Fortune’s yardarm for months.
His reign ended in the winter of 1722 when the English warship HMS Swallow caught up to him. In a daring confrontation, Roberts was mortally wounded by grapeshot to the throat. True to his wishes, his crew cast his body overboard, and despite exhaustive searches, his remains were never recovered.
Roberts’ legacy endures as a symbol of audacious piracy, his daring tactics and sheer audacity inspiring countless tales of high‑seas adventure.
1 Stenka Razin
Stenka Razin, a Cossack rebel and pirate of the mid‑1600s, remains a beloved folk hero throughout Russia. Historically, Cossacks enjoyed a degree of autonomy, but early 17th‑century policies tightened tsarist control, imposing harsh taxes and punishments.
Razin, a longtime community leader, was driven to vengeance after the execution of his brother by Russian troops. He rallied a force of 1,000 Don Cossacks, seized a fleet of tsarist ships, and began a campaign of plundering merchant vessels and liberating political prisoners along the Volga River.
His daring exploits elevated him to a peasant champion, inspiring uprisings across the Russian lands. As his army swelled beyond 2,000, Razin expanded his raids to the Caspian Sea and the Persian coast, cementing his reputation as a formidable maritime insurgent.
In 1671, Razin plotted a bold capture of Simbirsk but was betrayed by his own men. Captured and taken to Moscow, he endured four days of brutal torture before being executed. Despite his death, his legend persisted, with Cossack rebels continuing to resist Russian oppression, their stories and songs preserving Razin’s memory.
Alyssa Howard is a freelance writer and history fanatic. You can see her work at www.kitfoxsociety.wordpress.com.